CN104650299B - A kind of button unsaturated polyester resin and preparation method thereof - Google Patents
A kind of button unsaturated polyester resin and preparation method thereof Download PDFInfo
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- CN104650299B CN104650299B CN201510052112.6A CN201510052112A CN104650299B CN 104650299 B CN104650299 B CN 104650299B CN 201510052112 A CN201510052112 A CN 201510052112A CN 104650299 B CN104650299 B CN 104650299B
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Abstract
The invention discloses a kind of button unsaturated polyester resins and preparation method thereof, which is mainly made of the component of following parts by weight：1000~1800 parts by weight of phthalic anhydride, 800~1500 parts by weight of cis-butenedioic anhydride, 1,2 propylene glycol, 600~1300 parts by weight, 300~800 parts by weight of ethylene glycol, 1000~1800 parts by weight of dipropylene glycol, 2000~3500 parts by weight of styrene, 1~3 parts by weight of polymerization inhibitor, 1~3 parts by weight of antioxidant, 0.01~0.05 parts by weight of retarder；Wherein, the polymerization inhibitor is high temperature polymerization inhibitor and low temperature polymerization inhibitor.Compared with the prior art, button unsaturated polyester resin of the present invention had not only met the requirement of European Union environmental protection regulation but also had been suitable for button technological requirement.
Description
Technical field
The invention belongs to chemical fields, and in particular to a kind of button unsaturated polyester resin and preparation method thereof.
Background technology
Unsaturated polyester resin (Unsaturated Polyester Resins, abbreviation UPR) has function groups
Chain macromolecule compound has polyester chain link and unsaturated double-bond on its skeleton main chain, and in each band in macromolecular chain both ends
There are carboxyl and hydroxyl.The use of the maximum benefit of unsaturated polyester resin being its diluent (styrene) in last use will be with
Double bond on main chain is copolymerized cross-linking reaction, so the volatile quantity of solvent is less during use, thus belongs to environmental protection
A kind of product, the most important casting of unsaturated polyester resin are applied as manufacture button product.Button tree currently on the market
Fat all uses the formula of high activity, while plasticizer is added to offset the brittleness brought due to high activity.But with European Union's ring
The successive appearance for protecting regulation, limits use of the plasticizer in button resin.In addition, in the manufacturing process of button, in water
The phenomenon that water suction being easy when middle slice and button is caused to whiten.
Invention content
It is an object of the present invention to overcome the above deficiencies, provides a kind of requirement not only having met European Union environmental protection regulation but also suitable
Together in the button unsaturated polyester resin of button technological requirement.The button unsaturated polyester resin is meeting button making work
Under the premise of skill demand, the water imbibition of casting resin is reduced, and there is certain toughness, meet slice and the need of punching
It wants.
It is a further object of the present invention to provide the preparation methods of above-mentioned button unsaturated polyester resin.
The purpose of the present invention is what is be accomplished by the following way：
A kind of button unsaturated polyester resin, the resin are mainly made of the raw material of following parts by weight：
1000~1800 parts by weight of phthalic anhydride, 800~1500 parts by weight of cis-butenedioic anhydride, 600~1300 parts by weight of 1,2-PD, second
300~800 parts by weight of glycol, 1000~1800 parts by weight of dipropylene glycol, 2000~3500 parts by weight of styrene, polymerization inhibitor 1~3
Parts by weight, 1~3 parts by weight of antioxidant, 0.01~0.05 parts by weight of retarder；Wherein, the polymerization inhibitor is high temperature polymerization inhibitor
With low temperature polymerization inhibitor.
Above-mentioned button is preferably mainly made of the raw material of following parts by weight with unsaturated polyester resin：
1400~1800 parts by weight of phthalic anhydride, 900~1300 parts by weight of cis-butenedioic anhydride, 600~1000 parts by weight of 1,2-PD, second
500~800 parts by weight of glycol, 1100~1400 parts by weight of dipropylene glycol, 2000~2300 parts by weight of styrene, polymerization inhibitor 1~2
Parts by weight, 1~2 parts by weight of antioxidant, 0.01~0.02 parts by weight of retarder；Wherein, the polymerization inhibitor is high temperature polymerization inhibitor
With low temperature polymerization inhibitor.
Above-mentioned button is further preferably mainly made of the raw material of following parts by weight with unsaturated polyester resin：
1500~1700 parts by weight of phthalic anhydride, 1000~1200 parts by weight of cis-butenedioic anhydride, 700~900 parts by weight of 1,2-PD, second
500~700 parts by weight of glycol, 1100~1300 parts by weight of dipropylene glycol, 2100~2200 parts by weight of styrene, polymerization inhibitor 1~
1.5 parts by weight, 1~1.5 parts by weight of antioxidant, 0.01~0.02 parts by weight of retarder；Wherein, the polymerization inhibitor hinders for high temperature
Poly- agent and low temperature polymerization inhibitor.
The resin also adds toner and fluorescent whitening agent as auxiliary material, and the two weight ratio is 8~12：1~5, preferably
Weight ratio 10：3, addition is the 0.0001~0.001% of raw material total amount, using conventional toner and fluorescent whitening agent.
Above-mentioned button is most preferably mainly made of the raw material of following parts by weight with unsaturated polyester resin：
1600 parts by weight of phthalic anhydride, 1100 parts by weight of cis-butenedioic anhydride, 800 parts by weight of 1,2-PD, 600 parts by weight of ethylene glycol, two
1200 parts by weight of propylene glycol, 2200 parts by weight of styrene, 0.5 parts by weight of hydroquinone, 0.7 parts by weight of methylnaphthohydroquinone, phosphorous acid
1.5 parts by weight of triphenylmethyl methacrylate, 0.01 parts by weight of copper naphthenate, 0.05 parts by weight of toner, 0.015 parts by weight of fluorescent whitening agent.
The preferred hydroquinone of high temperature polymerization inhibitor of the present invention, the preferred methylnaphthohydroquinone of low temperature polymerization inhibitor；High temperature polymerization inhibitor
Weight ratio with low temperature polymerization inhibitor is 3-6：6-9, preferred weight ratio 5：7.The preferred triphenyl phosphite of the antioxidant delays
The poly- preferred copper naphthenate of agent.
The preparation method of above-mentioned button unsaturated polyester resin includes the following steps：
A) by phthalic anhydride, cis-butenedioic anhydride, 1,2-PD, ethylene glycol, after dipropylene glycol and high temperature polymerization inhibitor, antioxidant mixing
1~2h is warming up to water outlet, then is warming up to 210~215 DEG C with the speed of 8~10 DEG C/h, keeps the temperature 4~5h, material acid value up to 68~
72mgKOH/g vacuumizes decompression, and vacuum degree maintains 2h~5h up to 0.92atm or more, until acid value stops up to 28~35mgKOH/g
It vacuumizes, is cooled to 180 DEG C, low temperature polymerization inhibitor is added, is down to 70~90 DEG C and obtains unsaturated polyester resin；
B) unsaturated polyester resin of acquirement is slowly added into the mixing of styrene and retarder under the conditions of 70~80 DEG C
It in object, stirs evenly, 2~3h adds whole unsaturated polyester resins, then is cooled to 40~45 DEG C, stirs 30min or more.
The preparation method of button unsaturated polyester resin can also be prepared by following steps：
A) by phthalic anhydride, cis-butenedioic anhydride, 1,2-PD, ethylene glycol, after dipropylene glycol and high temperature polymerization inhibitor, antioxidant mixing
1~2h is warming up to water outlet, then is warming up to 210~215 DEG C with the speed of 8~10 DEG C/h, keeps the temperature 4~5h, material acid value up to 68~
72mgKOH/g vacuumizes decompression, and vacuum degree maintains 2h~5h up to 0.92atm or more, until acid value stops up to 28~35mgKOH/g
It vacuumizes, is cooled to 180 DEG C, low temperature polymerization inhibitor and paraffin is added, is down to 70~90 DEG C and obtains unsaturated polyester resin；
B) unsaturated polyester resin of acquirement is slowly added into styrene, retarder, toner under the conditions of 70~80 DEG C
And in the mixture of fluorescent whitening agent, stir evenly, 2~3h adds whole unsaturated polyester resins, then is cooled to 40~45
DEG C, stir 30min or more.
The button that the present invention obtains can also be cured with unsaturated polyester resin, and gel time is controlled in 30~40min.
Conventional accelerating agent, curing agent etc. are added when solidification, casting is made according to the requirement of " making of sample " in GB/T8237-2005
Body.
Unsaturated polyester resin of the present invention is the high score made of unsaturated dibasic acid (cis-butenedioic anhydride) and dihydric alcohol polycondensation
Sub- compound, water imbibition is big in existing button resin, it usually needs a large amount of dibutyl phthalate is added.The present invention
Dipropylene glycol and unsaturated acids is added simultaneously, reduces the reactivity of resin formula, significantly reduces water imbibition, while not adding
Under the premise of plasticizer, obtains button and punch required toughness.
In addition, the present invention prevents inappropriate polymerization using suitable polymerization inhibitor and specific feed postition and influences to react
Speed.Moreover, in preparation process, middle control acid value is preferably between 68~72mgKOH/g, if acid value is excessively high, free acid or acid
It is more, it is easy to be lost in；If acid value is too low, can waste time significantly.The present invention uses a certain amount of dipropylene glycol, can make
Obtaining product reduces water imbibition, prevents " white edge " phenomenon when button manufacture.
Beneficial effects of the present invention compared with the prior art：
(1) button can be sliced in water with resin or punching is without generating the phenomenon that water suction is whitened.
(2) there is suitable toughness, slice is not broken, and punching does not rupture.
(3) meet in European Union environmental protection regulation to the content requirement of various limitation substances.
Button resin of the present invention reaches claimed below：Naval stores casting matrix water absorption rate is less than 0.15%, naval stores
The tensile property of casting matrix：Tensile strength is more than 50MPa, and tensile modulus of elasticity is more than 2.3GPa, and elongation at break is more than
9.5%.
Specific implementation mode
It is further illustrated the present invention below by way of specific embodiment.But the detail of embodiment is only used for explaining this hair
It is bright, it should not be construed as limited overall technical solution.
Embodiment 1
Formula：1600 parts by weight of phthalic anhydride, 1100 parts by weight of cis-butenedioic anhydride, 800 parts by weight of 1,2-PD, 600 weight of ethylene glycol
Part, 1200 parts by weight of dipropylene glycol, 2200 parts by weight of styrene, 0.5 parts by weight of hydroquinone, 0.7 parts by weight of methylnaphthohydroquinone, Asia
1.5 parts by weight of triphenyl phosphate, 0.01 parts by weight of copper naphthenate, 0.05 parts by weight of toner, 0.015 weight of fluorescent whitening agent
Part.
The preparation method of button unsaturated polyester resin is：
A) by phthalic anhydride, cis-butenedioic anhydride, 1,2-PD, ethylene glycol, after dipropylene glycol and high temperature polymerization inhibitor, antioxidant mixing
1~2h is warming up to water outlet, then is warming up to 210 DEG C with the speed of 8~10 DEG C/h, keeps the temperature 5h, and material acid value reaches 68mgKOH/g, takes out
Vacuum decompression, vacuum degree maintain 5h up to 0.92atm or more, until acid value reaches 35mgKOH/g, stop vacuumizing, are cooled to 180 DEG C,
Low temperature polymerization inhibitor is added, is down to 80 DEG C and obtains unsaturated polyester resin；
B) unsaturated polyester resin of acquirement is slowly added into styrene, retarder, toner and glimmering under the conditions of 70 DEG C
It in the mixture of optical brightener, stirs evenly, 2h adds whole unsaturated polyester resins, then is cooled to 45 DEG C, stirring
30min。
The cobalt iso-octoate of the resin 100g and 2g that obtain and the cyclohexanone peroxide of 2g become after gel 40min solid
Body, room temperature 24 hours are dried 3 hours at 60 DEG C, and 110 DEG C of conditions are dried 1 hour, and casting is made in room temperature after 24 hours
Body, this method are that casting matrix is made according to the custom requirements of " making of sample " in GB/T8237/2005.
Embodiment 2
Formula：1500 parts by weight of phthalic anhydride, 1200 parts by weight of cis-butenedioic anhydride, 900 parts by weight of 1,2-PD, 700 weight of ethylene glycol
Part, 1300 parts by weight of dipropylene glycol, 2100 parts by weight of styrene, 0.6 parts by weight of hydroquinone, 0.9 parts by weight of methylnaphthohydroquinone, Asia
1.5 parts by weight of triphenyl phosphate, 0.02 parts by weight of copper naphthenate；
The preparation method of button unsaturated polyester resin is：
A) by phthalic anhydride, cis-butenedioic anhydride, 1,2-PD, ethylene glycol, after dipropylene glycol and high temperature polymerization inhibitor, antioxidant mixing
It is warming up to water outlet in 1~2h, then 215 DEG C are warming up to the speed of 8~10 DEG C/h, keeps the temperature 4h, material acid value reaches 72mgKOH/g,
Decompression is vacuumized, vacuum degree maintains 4h up to 0.92atm or more, until acid value reaches 30mgKOH/g, stops vacuumizing, is cooled to 180
DEG C, low temperature polymerization inhibitor is added, is down to 90 DEG C and obtains unsaturated polyester resin；
B) unsaturated polyester resin of acquirement is slowly added under the conditions of 80 DEG C in the mixture of styrene, retarder,
It stirs evenly, 3h adds whole unsaturated polyester resins, then is cooled to 40 DEG C, stirs 30min or more.
The cobalt iso-octoate of the resin 100g resins and 2g that obtain and the cyclohexanone peroxide of 2g, after gel 40min at
For solid, room temperature 24 hours is dried 3 hours at 60 DEG C, and 110 DEG C of conditions are dried 1 hour, and room temperature is made after 24 hours
Casting matrix, this method are that casting matrix is made according to the custom requirements of " making of sample " in GB/T8237/2005.
Embodiment 3
Formula：1700 parts by weight of phthalic anhydride, 1000 parts by weight of cis-butenedioic anhydride, 700 parts by weight of 1,2-PD, 500 weight of ethylene glycol
Part, 1100 parts by weight of dipropylene glycol, 2300 parts by weight of styrene, 0.4 parts by weight of hydroquinone, 0.7 parts by weight of methylnaphthohydroquinone, Asia
1 parts by weight of triphenyl phosphate, 0.05 parts by weight of copper naphthenate；
The preparation method of button unsaturated polyester resin is：
A) by phthalic anhydride, cis-butenedioic anhydride, 1,2-PD, ethylene glycol, after dipropylene glycol and high temperature polymerization inhibitor, antioxidant mixing
It is warming up to water outlet in 1~2h, then 210 DEG C are warming up to the speed of 8~10 DEG C/h, keeps the temperature 4h, material acid value reaches 70mgKOH/g,
Decompression is vacuumized, vacuum degree maintains 2h up to 0.92atm or more, until acid value reaches 28mgKOH/g, stops vacuumizing, is cooled to 180
DEG C, low temperature polymerization inhibitor is added, is down to 70 DEG C and obtains unsaturated polyester resin；
B) unsaturated polyester resin of acquirement is slowly added under the conditions of 70 DEG C in the mixture of styrene, retarder,
It stirs evenly, 2.5h adds whole unsaturated polyester resins, then is cooled to 40 DEG C, stirs 30min or more.
The cobalt iso-octoate of the resin 100g resins and 2g that obtain and the cyclohexanone peroxide of 2g, after gel 40min at
For solid, room temperature 24 hours is dried 3 hours at 60 DEG C, and 110 DEG C of conditions are dried 1 hour, and room temperature is made after 24 hours
Casting matrix, this method are that casting matrix is made according to the custom requirements of " making of sample " in GB/T8237/2005.Embodiment 4
Formula：1400 parts by weight of phthalic anhydride, 1300 parts by weight of cis-butenedioic anhydride, 600 parts by weight of 1,2-PD, 800 weight of ethylene glycol
Part, 1100 parts by weight of dipropylene glycol, 2900 parts by weight of styrene, 0.5 parts by weight of hydroquinone, 0.7 parts by weight of methylnaphthohydroquinone, Asia
1.5 parts by weight of triphenyl phosphate, 0.01 parts by weight of copper naphthenate, 0.05 parts by weight of toner, 0.03 parts by weight of fluorescent whitening agent.
The preparation method is the same as that of Example 1.
Embodiment 5
Formula：1800 parts by weight of phthalic anhydride, 900 parts by weight of cis-butenedioic anhydride, 900 parts by weight of 1,2-PD, 500 weight of ethylene glycol
Part, 1400 parts by weight of dipropylene glycol, 2500 parts by weight of styrene, 0.5 parts by weight of hydroquinone, 0.7 parts by weight of methylnaphthohydroquinone, Asia
2 parts by weight of triphenyl phosphate, 0.05 parts by weight of copper naphthenate, 0.05 parts by weight of toner, 0.02 parts by weight of fluorescent whitening agent.
The preparation method is the same as that of Example 1.
It is prepared that material can be sliced in water or punching is whitened without generating water suction according to Examples 1 to 5 method
Phenomenon has suitable toughness, and slice is not broken, and punching does not rupture, and meets in European Union environmental protection regulation to various limitation substances
Content requirement.Performance detection data is as shown in table 1：
Table 1
Conventional production process and process is not described in detail in the present invention, and detailed specific method and process are in combination with above-mentioned
Production method and conventional method are implemented, and person of ordinary skill in the field is fully able to repeat to realize.
Claims (7)
1. a kind of button unsaturated polyester resin, it is characterised in that the resin is mainly made of the raw material of following parts by weight：
1400~1800 parts by weight of phthalic anhydride, 900~1300 parts by weight of cis-butenedioic anhydride, 600~1000 parts by weight of 1,2-PD, ethylene glycol
500~800 parts by weight, 1100~1400 parts by weight of dipropylene glycol, 2000~2300 parts by weight of styrene, 1~2 weight of polymerization inhibitor
Part, 1~2 parts by weight of antioxidant, 0.01~0.02 parts by weight of retarder；Wherein, the polymerization inhibitor is high temperature polymerization inhibitor and low
Warm polymerization inhibitor, the high temperature polymerization inhibitor are hydroquinone, and the low temperature polymerization inhibitor is methylnaphthohydroquinone；High temperature polymerization inhibitor and low
The weight ratio of warm polymerization inhibitor is 3~6：6~9.
2. button unsaturated polyester resin according to claim 1, it is characterised in that the resin is mainly by following weight
The raw material of part is made：
1500~1700 parts by weight of phthalic anhydride, 1000~1200 parts by weight of cis-butenedioic anhydride, 700~900 parts by weight of 1,2-PD, ethylene glycol
500~700 parts by weight, 1100~1300 parts by weight of dipropylene glycol, 2100~2200 parts by weight of styrene, 1~1.5 weight of polymerization inhibitor
Measure part, 1~1.5 parts by weight of antioxidant, 0.01~0.02 parts by weight of retarder；Wherein, the polymerization inhibitor is high temperature polymerization inhibitor
With low temperature polymerization inhibitor.
3. button unsaturated polyester resin according to claim 1 or 2, it is characterised in that the resin also adds toner
And fluorescent whitening agent, the two weight ratio are 8~12：1~5, addition is the 0.0001~0.001% of raw material total amount.
4. button unsaturated polyester resin according to claim 1 or 2, it is characterised in that the antioxidant is phosphorous
Triphenyl phosphate ester.
5. according to claims 1 or 2 or the button unsaturated polyester resin, it is characterised in that the retarder is ring
Alkanoic acid copper.
6. a kind of preparation method of button unsaturated polyester resin as claimed in claim 1 or 2, it is characterised in that this method packet
Include following steps：
A) by phthalic anhydride, cis-butenedioic anhydride, 1,2-PD, ethylene glycol, after dipropylene glycol and high temperature polymerization inhibitor, antioxidant mixing 1~
2h is warming up to water outlet, then is warming up to 210~215 DEG C with the speed of 8~10 DEG C/h, keeps the temperature 4~5h, material acid value up to 68~
72mgKOH/g vacuumizes decompression, and vacuum degree maintains 2h~5h up to 0.92atm or more, until acid value stops up to 28~35mgKOH/g
It vacuumizes, is cooled to 180 DEG C, low temperature polymerization inhibitor is added, is down to 70~90 DEG C and obtains unsaturated polyester resin；
B) unsaturated polyester resin of acquirement is slowly added under the conditions of 70~80 DEG C in the mixture of styrene and retarder,
It stirs evenly, 2~3h adds whole unsaturated polyester resins, then is cooled to 40~45 DEG C, stirs 30min or more.
7. a kind of preparation method of the button unsaturated polyester resin described in claim 3, it is characterised in that this method includes
Following steps：
A) by phthalic anhydride, cis-butenedioic anhydride, 1,2-PD, ethylene glycol, after dipropylene glycol and high temperature polymerization inhibitor, antioxidant mixing 1~
2h is warming up to water outlet, then is warming up to 210~215 DEG C with the speed of 8~10 DEG C/h, keeps the temperature 4~5h, material acid value up to 68~
72mgKOH/g vacuumizes decompression, and vacuum degree maintains 2h~5h up to 0.92atm or more, until acid value stops up to 28~35mgKOH/g
It vacuumizes, is cooled to 180 DEG C, low temperature polymerization inhibitor is added, is down to 70~90 DEG C and obtains unsaturated polyester resin；
B) unsaturated polyester resin of acquirement is slowly added into styrene, retarder, toner and glimmering under the conditions of 70~80 DEG C
It in the mixture of optical brightener, stirs evenly, 2~3h adds whole unsaturated polyester resins, then is cooled to 40~45 DEG C, stirs
Mix 30min or more.
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101911411B1 (en) | 2017-11-07 | 2018-10-25 | 애경화학 주식회사 | Unsaturated polyester resin for apparel button having high impact resistance and the method of manufacturing the same |
| CN109957097A (en) * | 2017-12-25 | 2019-07-02 | 宜兴市兴南复合材料厂有限公司 | A kind of button unsaturated-resin and preparation process |
| CN108384463A (en) * | 2018-02-07 | 2018-08-10 | 袁林林 | A kind of heat-resistant adhesive and preparation method thereof |
| CN110305438A (en) * | 2019-07-17 | 2019-10-08 | 嘉善鼎兴服饰辅料有限公司 | A kind of resin button and its production technology of corrosion-and high-temp-resistant |
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| CN1117976A (en) * | 1994-06-21 | 1996-03-06 | 和歌山县 | Method and apparatus for recovery unsaturated polyester resin waste |
| CN101570589A (en) * | 2008-12-30 | 2009-11-04 | 上海新天和树脂有限公司 | Method for preparing environment-friendly unsaturated polyester resin and product and application thereof |
| CN102585107A (en) * | 2012-03-09 | 2012-07-18 | 宜兴市兴合树脂有限公司 | Unsaturated polyester resin for button and preparation method thereof |
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| CN102585106B (en) * | 2012-03-08 | 2014-01-29 | 宜兴市兴合树脂有限公司 | Unsaturated polyester resin for die pressing and preparation method thereof |
| CN102603992B (en) * | 2012-03-08 | 2014-04-16 | 宜兴市兴合树脂有限公司 | Unsaturated polyester resin for pultrusion and preparation method for same |
| CN103275309A (en) * | 2013-06-26 | 2013-09-04 | 兰州理工大学 | Phosphorous flame-retardant unsaturated polyester resin and preparation method thereof |
| CN103275277A (en) * | 2013-06-26 | 2013-09-04 | 兰州理工大学 | Unsaturated polyester resin flame-retardant material and preparation method thereof |
| CN103833919B (en) * | 2014-02-11 | 2016-04-13 | 漳州亚邦化学有限公司 | A kind of air-dried unsaturated polyester resin and production method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1117976A (en) * | 1994-06-21 | 1996-03-06 | 和歌山县 | Method and apparatus for recovery unsaturated polyester resin waste |
| CN101570589A (en) * | 2008-12-30 | 2009-11-04 | 上海新天和树脂有限公司 | Method for preparing environment-friendly unsaturated polyester resin and product and application thereof |
| CN102585107A (en) * | 2012-03-09 | 2012-07-18 | 宜兴市兴合树脂有限公司 | Unsaturated polyester resin for button and preparation method thereof |
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